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Terconazole

Terconazole structure

CAS No:
67915-31-5
Formula:
C26H31Cl2N5O3
Chemical Name:
Terconazole
Synonyms:
Piperazine,1-[4-[[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-4-(1-methylethyl)-,rel-;Piperazine,1-[4-[[2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-4-(1-methylethyl)-,cis-;rel-1-[4-[[(2R,4S)-2-(2,4-Dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-4-(1-methylethyl)piperazine;Triaconazole;Terconazole;Gyno-Terazol;Terazol;Terazol Cream & Suppositories;R 42470;Fungistat;Tercospor;NSC 331942;(±)-Terconazole;Termayazole;85058-79-3
Categories:
Analytical Chemistry > Standard

Description

Terconazole is a broad-spectrum antifungal medication for the treatment of vaginal yeast infection.

Solid

(2R,4S)-terconazole is a 1-(4-{[2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)-4-isopropylpiperazine in which positions 2 and 4 of the 1,3-dioxolane moiety have R and S configuration, respectively. It is an enantiomer of a (2S,4R)-terconazole.|Terconazole is an anti-fungal drug that is mainly used to treat vaginal yeast infections (or vaginal candidiasis). It is classified as a triazole ketal derivative. Terconazole was initially approved by the FDA in 1987. This drug is available in cream and suppository forms and both have demonstrated high levels of safety, efficacy, and tolerability in clinical trials.

Terconazole Basic Attributes

Molecular Weight：

532.46

Exact Mass：

532.46

EC Number：

267-751-6

NSC Number：

760361

DSSTox ID：

DTXSID2045498

ATC Code：

G - Genito urinary system and sex hormones

HScode：

2934990002

Characteristics

PSA：

64.9

XLogP3：

4.8

Appearance：

white

Density：

1.35g/cm3

Melting Point：

126.3 °C

Boiling Point：

681.8°C at 760 mmHg

Flash Point：

366.2ºC

Refractive Index：

1.64

Water Solubility：

DMSO: soluble 1mg/mL

Storage Conditions：

2-8°C

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

36/37/38-53

safety instructions：

RTECS Number：

TL3564600

Marks：

Precautionary statement(s)：

P305 + P351 + P338

Hazard Statements：

H315-H319-H335-H413

GHS Classification：

|Warning|H302 (59.57%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P273, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 94 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Toxicity

Toxicity Summary：

The oral LD50 values were found to be 1741 and 849 mg/kg for the male and female in rat.

Protein Binding：

94.9%

Drug Information

Drug Indication：

For the treatment of candidiasis (a yeast-like fungal infection) of the vulva and vagina.|FDA Label

Pharmacology：

Terconazole is a triazole antifungal agent available for intravaginal use. It is structurally related to imidazole-derivative antifungal agents, although terconazole and other triazoles have 3 nitrogens in the azole ring. By inhibiting the 14-alpha-demethylase (lanosterol 14-alpha-demethylase), Terconazole inhibits ergosterol synthesis. Depletion of ergosterol in fungal membrane disrupts the structure and many functions of fungal membrane leading to inhibition of fungal growth.

MeSH：

Substances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues. (See all compounds classified as Antifungal Agents.)

Absorption：

Following intravaginal administration of terconazole in humans, absorption ranged from 5-8% in three hysterectomized subjects and 12-16% in two non-hysterectomized subjects with tubal ligations|Following oral (30 mg) administration of 14C-labelled terconazole, excretion of radioactivity was both by renal (32-56%) and fecal (47-52%) routes.

Metabolism/Metabolites：

Systemically absorbed drug appears to be rapidly and extensively metabolized. Terconazole primarily undergoes oxidatative N- and O-dealkylation, dioxolane ring cleavage, and conjugation.

Biological Half-Life：

6.9 hours (range 4.0-11.3)

Mechanism of Action：

Terconazole may exert its antifungal activity by disrupting normal fungal cell membrane permeability. Terconazole and other triazole antifungal agents inhibit cytochrome P450 14-alpha-demethylase in susceptible fungi, which leads to the accumulation of lanosterol and other methylated sterols and a decrease in ergosterol concentration. Depletion of ergosterol in the membrane disrupts the structure and function of the fungal cell leading to a decrease or inhibition of fungal growth.

MeSH Entry Terms：

1-(4-((2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl)methoxy)phenyl)-4-(1-methylethyl)piperazine

Terconazole Use and Manufacturing

Uses

Terazol (Ortho-McNeil).

Use Classification：

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

Computed Properties

Molecular Weight:532.5
XLogP3:4.8
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:8
Exact Mass:531.1803953
Monoisotopic Mass:531.1803953
Topological Polar Surface Area:64.9
Heavy Atom Count:36
Complexity:693
Defined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Drug Function and Efficacy

Extract from the above information

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

Terconazole
Manufacturer	Wichita, Its Group of Pharmaceutical Co., Ltd.

Terconazole vaginal suppository
Ingredients	Terconazole.
Indication	Drug interactions may occur if used with other drugs. Please consult your doctor or pharmacist for details.
Specifications	80mg

Terconazole
Manufacturer	Wichita, Its Group of Pharmaceutical Co., Ltd.

Registered Holders

W R GRACE AND CO -CONN

United States
Active
QUIMICA SINTETICA SA

Spain
Active
Shanghai Shyndec Pharmaceutical Co., Ltd.

China
Active

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